3-[3-(5-Isopropyl-2,6-dimethoxy-pyrimidine-4-carbonyl)-5-methyl-phenyl]-acrylonitrile → 3-[3-(5-Isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-phenyl]-acrylonitrile

HRID 426170Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 426170
[CH:1]([C:4]1[C:5]([C:14]([C:16]2[CH:17]=[C:18]([CH:23]=[CH:24][C:25]#[N:26])[CH:19]=[C:20]([CH3:22])[CH:21]=2)=[O:15])=[N:6][C:7]([O:12]C)=[N:8][C:9]=1[O:10]C)([CH3:3])[CH3:2]>C1COCC1.C(Cl)(=O)C(Cl)=O>[CH:1]([C:4]1[C:9](=[O:10])[NH:8][C:7](=[O:12])[NH:6][C:5]=1[C:14]([C:16]1[CH:17]=[C:18]([CH:23]=[CH:24][C:25]#[N:26])[CH:19]=[C:20]([CH3:22])[CH:21]=1)=[O:15])([CH3:3])[CH3:2]

Komponenten

4

Edukt 1

HCID 667055443-[3-(5-Isopropyl-2,6-dimethoxy-pyrimidine-4-carbonyl)-5-methyl-phenyl]-acrylonitrile

Produkt 1

HCID 667053903-[3-(5-Isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-phenyl]-acrylonitrileAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 65578Oxalyl chlorideLösungsmittel

Versuchsvorschrift

To a stirred solution of 3-[3-(5-Isopropyl-2,6-dimethoxy-pyrimidine-4-carbonyl)-5-methyl-phenyl]-acrylonitrile (5.36 g, 15.27 mmol) in anhydrous THF (50 ml), oxalyl chloride (25 ml) was added. The mixture was then refluxed with vigorous stirring for overnight. After cooling to room temperature, the mixture was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, EA: hexanes (from 1:1 to 4:1)) to afford 2.7 g (55%) of a white solid. m.p. 233-235° C.; 1H NMR (300 MHz, CD3OD/CDCl3) δ 1.16 (6H, d, J=6.9 Hz), 2.39-2.56 (4H, m), 6.12 (1H, d, J=16.6 Hz), 7.49 (1H, d, J=16.6 Hz), 7.66 (1H, s), 7.83 (1H, s), 7.87 (1H, s); m/z (LC/Mass, EI) 324 (M+H+).

Aufarbeitung

  1. temperatureThe mixture was then refluxed
  2. customthe mixture was evaporated in vacuo
  3. customthe residue was purified by silica gel column chromatography (eluent, EA: hexanes (from 1:1 to 4:1))

Quellen und Nachweise

ORD-Eintrag
ord-8647082309ae4ca78220a5b849fc5f1e
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106064B2

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